The prior art shows the use of trifluoromethanesulfonic acid (triflic) acid as a catalyst for various hydrocarbon conversion processes but such prior art fails to suggest the instant invention. Some prior art patents involving the use of triflic acid as a catalyst or the preparation of condensation products from a diene and a hydroxyaryl are set forth below.
U.S. Pat. No. 4,973,764 of Nov. 27,1990 to A. Oswald et al discloses the use of triflic acid as an alkoxylation catalyst.
U.S. Pat. No. 5,521,260 of May 28, 1996 to N. Futaesaku et al discloses the use of triflic acid as a polymerization catalyst for thermosetting resins.
U.S. Pat. No. 5,607,890 of Mar. 4, 1997 to F. J. Chen et al discloses heterogeneous catalysts having certain insoluble triflic acid salts on an inorganic oxide support for catalyzing hydrocarbon conversion reactions including alkylation and polymerization. As suitable monomers for the conversion reactions a wide variety of olefins and carbocyclic aromatic compounds are mentioned. Monomer feed streams for polymerization are substantially free of impurities which may adversely affect polymerization such as basic and nitrogen materials. Lower alcohols along with organic acids are mentioned as catalyst promoters.
U.S. Pat. No. 5,663, 470 of Sep. 2, 1997 to F. Chen et al discloses a heterogeneous catalyst system comprising a solid state insoluble salt catalyst for polymerization and alkylation of olefinic monomers in the presence of a polar or non-polar reaction medium which comprises: (a) a solid state catalyst component of at least one salt of a strong acid and certain transition metals wherein the salt is insoluble in the reaction medium; and (b) a cocatalyst for promoting the polymerization. The salt of a strong acid includes that of triflic acid. Monomers include a wide variety of olefins and carbocyclic aromatic compounds. The enumeration of cocatalyst includes water, alcohols such as the lower alkanols, e.g., methanol, and Bronsted acids such as triflic acid or Lewis acids. This 470 patent of Chen et al describes triflic acid, water and methanol as catalyst reaction promoters. However, in, the catalyst system of the instant invention, water and alcohols, e.g., methanol are catalyst suppressors in that water and methanol both act as catalyst retarders instead of promoters. Although the applicant does not wish to be held to any theory, it is believed that water as well as methanol in contact with the insoluble catalyst salts of Chen et al cause dissociation of the salts which in turn promote the catalytic reaction.
3M Product Information Bulletin of 6-95 entitled "Fluorochem" discloses various properties and uses of triflic acid, e.g., the use of triflic acid as a catalyst in alkylation and polymerization reactions as well as some physical or chemical properties of mixtures of triflic acid with water or ethers.
Neftekhimiya, 1974, Volume XIV, No. 2, 280-283 (Russian) discloses the reaction of phenol with clicyclopentadiene in the presence of about 10% to 50% by weight, based on the weight of both monomers, of a cation exchange resin catalyst for the preparation of compounds, such as prepared in the instant invention, including some resin.
H. A. Bruson, et al., J. Amer. Chem. Soc. 68, 8 (1946), pp 8-10, shows the preparation of aryloxy-dicyclopentadiene compounds from hydroxyaryls and dicyclopentadiene in the presence of various acids.